Naphthalocyanine compounds, naphthalocyanine polymers and method for making
Novel naphthalocyanine compounds are provided including nitro- and amino-substituted naphthalocyanine compounds, and vinyl-containing naphthalocyanine compounds. The compounds have improved solubility and high purity and are expected to find use as photo-functional materials such as dyes. Polymers are obtained using the vinyl-containing naphthalocyanine compounds. The polymers also have improved solubility, high purity, a high naphthalocyanine content and ease of control of the orientation of naphthalocyanine rings and are expected of use as various functional materials.
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Claims
1. A method for preparing a naphthalocyanine compound of the following general formula (1): ##STR34## wherein each of Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 is a group of atoms to form a substituted or unsubstituted benzene ring or naphthalene ring fused to the adjacent pyrrole ring, at least one of the rings formed by Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 being a substituted or unsubstituted naphthalene ring,
- letter q is 0 or an integer of 1 to 4 when Q.sup.1 forms a benzene ring, or 0 or an integer of 1 to 6 when Q.sup.1 forms a naphthalene ring,
- M.sup.1 is a center atom,
- comprising the step of reacting a phthalonitrile compound system including at least one dicyanonaphthalene and optionally at least one phthalonitrile.
2. A method for preparing a naphthalocyanine compound comprising the steps of:
- reacting a phthalonitrile compound system including at least one of a substituted or unsubstituted phthalonitrile and a substituted or unsubstituted dicyanonaphthalene and at least one of a substituted or unsubstituted nitrophthalonitrile and a substituted or unsubstituted dicyanonitronaphthalene, thereby forming a nitro-substituted naphthalocyanine compound of the following general formula (2): ##STR35## wherein each of Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 is a group of atoms to form a substituted or unsubstituted benzene ring or naphthalene ring fused to the adjacent pyrrole ring, at least one of the rings formed by Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 being a naphthalene ring,
- reducing the nitro group of said nitro-substituted naphthalocyanine compound into an amino-substituted naphthalocyanine compound of the following general formula (3): ##STR36## wherein each of Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 is a group of atoms to form a substituted or unsubstituted benzene ring or naphthalene ring fused to the adjacent pyrrole ring, at least one of the rings formed by Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 being a substituted or unsubstituted naphthalene ring, and
- introducing an acryloyl group into the amino group of said amino-substituted naphthalocyanine compound to form a naphthalocyanine compound of the following general formula (4): ##STR37## wherein each of Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 is a group of atoms to form a benzene ring or naphthalene ring fused to the adjacent pyrrole ring, at least one of the rings formed by Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 being a naphthalene ring, and
- R.sup.5 is a hydrogen atom or an alkyl group.
3. A method for preparing a naphthalocyanine polymer comprising the step of polymerizing a naphthalocyanine compound of the following general formula (4): ##STR38## wherein each of Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 is a group of atoms to form a benzene ring or naphthalene ring fused to the adjacent pyrrole ring, at least one of the rings formed by Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 being a naphthalene ring, and
- R.sup.5 is a hydrogen atom or an alkyl group,
- to form a naphthalocyanine polymer having a structural unit of the following general formula (5): ##STR39## wherein each of Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 is a group of atoms to form a substituted or unsubstituted benzene ring or naphthalene ring fused to the adjacent pyrrole ring, at least one of the rings formed by Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 being a substituted or unsubstituted naphthalene ring, and
- R.sup.5 is a hydrogen atom or an alkyl group.
4. A method for preparing a naphthalocyanine compound comprising the step of substituting a metal for the two hydrogen atoms positioned centrally of the naphthalocyanine ring of a naphthalocyanine polymer having a structural unit of the following general formula (6): ##STR40## wherein each of Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 is a group of atoms to form a substituted or unsubstituted benzene ring or naphthalene ring fused to the adjacent pyrrole ring, at least one of the rings formed by Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 being a substituted or unsubstituted naphthalene ring,
- R.sup.5 is a hydrogen atom or an alkyl group, and
- M is a metal atom.
Type: Grant
Filed: Feb 25, 1997
Date of Patent: Jun 9, 1998
Assignees: Hirofusa Shirai (Nagano), TDK Corporation (Tokyo)
Inventors: Hirofusa Shirai (Nagano), Mutsumi Kimura (Ueda), Yuichi Kubota (Chiba)
Primary Examiner: Mukund J. Shah
Assistant Examiner: Pavanaram K. Sripada
Law Firm: Oblon, Spivak, McClelland, Maier & Neustadt, P.C.
Application Number: 8/806,156
International Classification: C07D48722; C09B 4704;
